Call Now:

Broker IDX Billing System

Broker,REALTOR ®,e-PRO
Broker IDX Sites Inc.
A Winning Team
  1. Home
  2. Property Search
  3. Search results
  4. 3435 Winding Oaks Drive 18, LONGBOAT KEY, FL 34228
Contact Broker IDX Sites Inc.
Contacting Broker IDX Sites Inc.
  • All fields are required.
Schedule A Showing
Schedule a Showing.
  • All fields are required.
Check this box to Register with us:
Submit an Offer Now!
Submit an Offer Now!
All fields are required.
Print Flyer
Active
Property Photos
3435 Winding Oaks Drive 18
  1. Image 1 of 85 For 3435 Winding Oaks Drive 18
  2. Image 2 of 85 For 3435 Winding Oaks Drive 18
  3. Image 3 of 85 For 3435 Winding Oaks Drive 18
  4. Image 4 of 85 For 3435 Winding Oaks Drive 18
  5. Image 5 of 85 For 3435 Winding Oaks Drive 18
  6. Image 6 of 85 For 3435 Winding Oaks Drive 18
  7. Image 7 of 85 For 3435 Winding Oaks Drive 18
  8. Image 8 of 85 For 3435 Winding Oaks Drive 18
  9. Image 9 of 85 For 3435 Winding Oaks Drive 18
  10. Image 10 of 85 For 3435 Winding Oaks Drive 18
  11. Image 11 of 85 For 3435 Winding Oaks Drive 18
  12. Image 12 of 85 For 3435 Winding Oaks Drive 18
  13. Image 13 of 85 For 3435 Winding Oaks Drive 18
  14. Image 14 of 85 For 3435 Winding Oaks Drive 18
  15. Image 15 of 85 For 3435 Winding Oaks Drive 18
  16. Image 16 of 85 For 3435 Winding Oaks Drive 18
  17. Image 17 of 85 For 3435 Winding Oaks Drive 18
  18. Image 18 of 85 For 3435 Winding Oaks Drive 18
  19. Image 19 of 85 For 3435 Winding Oaks Drive 18
  20. Image 20 of 85 For 3435 Winding Oaks Drive 18
  21. Image 21 of 85 For 3435 Winding Oaks Drive 18
  22. Image 22 of 85 For 3435 Winding Oaks Drive 18
  23. Image 23 of 85 For 3435 Winding Oaks Drive 18
  24. Image 24 of 85 For 3435 Winding Oaks Drive 18
  25. Image 25 of 85 For 3435 Winding Oaks Drive 18
  26. Image 26 of 85 For 3435 Winding Oaks Drive 18
  27. Image 27 of 85 For 3435 Winding Oaks Drive 18
  28. Image 28 of 85 For 3435 Winding Oaks Drive 18
  29. Image 29 of 85 For 3435 Winding Oaks Drive 18
  30. Image 30 of 85 For 3435 Winding Oaks Drive 18
  31. Image 31 of 85 For 3435 Winding Oaks Drive 18
  32. Image 32 of 85 For 3435 Winding Oaks Drive 18
  33. Image 33 of 85 For 3435 Winding Oaks Drive 18
  34. Image 34 of 85 For 3435 Winding Oaks Drive 18
  35. Image 35 of 85 For 3435 Winding Oaks Drive 18
  36. Image 36 of 85 For 3435 Winding Oaks Drive 18
  37. Image 37 of 85 For 3435 Winding Oaks Drive 18
  38. Image 38 of 85 For 3435 Winding Oaks Drive 18
  39. Image 39 of 85 For 3435 Winding Oaks Drive 18
  40. Image 40 of 85 For 3435 Winding Oaks Drive 18
  41. Image 41 of 85 For 3435 Winding Oaks Drive 18
  42. Image 42 of 85 For 3435 Winding Oaks Drive 18
  43. Image 43 of 85 For 3435 Winding Oaks Drive 18
  44. Image 44 of 85 For 3435 Winding Oaks Drive 18
  45. Image 45 of 85 For 3435 Winding Oaks Drive 18
  46. Image 46 of 85 For 3435 Winding Oaks Drive 18
  47. Image 47 of 85 For 3435 Winding Oaks Drive 18
  48. Image 48 of 85 For 3435 Winding Oaks Drive 18
  49. Image 49 of 85 For 3435 Winding Oaks Drive 18
  50. Image 50 of 85 For 3435 Winding Oaks Drive 18
  51. Image 51 of 85 For 3435 Winding Oaks Drive 18
  52. Image 52 of 85 For 3435 Winding Oaks Drive 18
  53. Image 53 of 85 For 3435 Winding Oaks Drive 18
  54. Image 54 of 85 For 3435 Winding Oaks Drive 18
  55. Image 55 of 85 For 3435 Winding Oaks Drive 18
  56. Image 56 of 85 For 3435 Winding Oaks Drive 18
  57. Image 57 of 85 For 3435 Winding Oaks Drive 18
  58. Image 58 of 85 For 3435 Winding Oaks Drive 18
  59. Image 59 of 85 For 3435 Winding Oaks Drive 18
  60. Image 60 of 85 For 3435 Winding Oaks Drive 18
  61. Image 61 of 85 For 3435 Winding Oaks Drive 18
  62. Image 62 of 85 For 3435 Winding Oaks Drive 18
  63. Image 63 of 85 For 3435 Winding Oaks Drive 18
  64. Image 64 of 85 For 3435 Winding Oaks Drive 18
  65. Image 65 of 85 For 3435 Winding Oaks Drive 18
  66. Image 66 of 85 For 3435 Winding Oaks Drive 18
  67. Image 67 of 85 For 3435 Winding Oaks Drive 18
  68. Image 68 of 85 For 3435 Winding Oaks Drive 18
  69. Image 69 of 85 For 3435 Winding Oaks Drive 18
  70. Image 70 of 85 For 3435 Winding Oaks Drive 18
  71. Image 71 of 85 For 3435 Winding Oaks Drive 18
  72. Image 72 of 85 For 3435 Winding Oaks Drive 18
  73. Image 73 of 85 For 3435 Winding Oaks Drive 18
  74. Image 74 of 85 For 3435 Winding Oaks Drive 18
  75. Image 75 of 85 For 3435 Winding Oaks Drive 18
  76. Image 76 of 85 For 3435 Winding Oaks Drive 18
  77. Image 77 of 85 For 3435 Winding Oaks Drive 18
  78. Image 78 of 85 For 3435 Winding Oaks Drive 18
  79. Image 79 of 85 For 3435 Winding Oaks Drive 18
  80. Image 80 of 85 For 3435 Winding Oaks Drive 18
  81. Image 81 of 85 For 3435 Winding Oaks Drive 18
  82. Image 82 of 85 For 3435 Winding Oaks Drive 18
  83. Image 83 of 85 For 3435 Winding Oaks Drive 18
  84. Image 84 of 85 For 3435 Winding Oaks Drive 18
  85. Image 85 of 85 For 3435 Winding Oaks Drive 18
Image Gallery

PRICED AT ONLY: $1,150,000

Address: 3435 Winding Oaks Drive 18, LONGBOAT KEY, FL 34228

Description

Own your own slice of tropical paradise on Longboat Key with this beautiful two bedroom two and on half bath Villa in the exclusive Winding Oaks Community located behind the gates of Bay Isles Association. Sweeping views of the Longboat Key Club Harbourside Golf Course and a sparkling inland waterway from your primary bedroom and expansive living/dining room combo that both exit through sliders to a fully enclosed wrap around deck to further enhance your tropical lifestyle. Open floor plan with soaring ceilings and enclosed atrium help to maximize the natural light and make the 2,555 sq feet feel even larger. Beautifully updated eat in kitchen with striking tray ceiling, ample pantry storage, bright white cabinets, quartz countertops and stainless steel appliances. Primary owners suite includes an designer walk in closet, updated bath with ceramic tile, walk in shower, double sinks and quartz counter tops. Split layout offers a private guest suite, with walk in closet, updated ensuite bathroom with ceramic tile, walk in shower and quartz counter tops. Large office with desk nook could easily be converted to another bedroom. Laundry room with storage and sink adjacent to large 2 car garage with epoxy floors and storage cabinets. Meticulously maintained, Impact Windows and sliders throughout, low maintenance mature plantings in private enclosed front courtyard. Dog friendly community. Beautiful updated community pool with bathrooms. Beach access via Bay Isles Beach Club which offers a private pavilion with bathrooms, volleyball, picnic tables, grills and ample parking. Low maintenance community where all exteriors and court yards are maintained by the association. Conveniently located mid key, one mile from Publix and CVS and a short drive to the restaurants and shops of St Armands and Downtown Sarasota.

Property Location and Similar Properties

All
Similar
Payment Calculator
  •   Principal & Interest -
  •   Property Tax $
  •   Home Insurance $
  •   HOA Fees $
  •   Mortgage Insurance-
  •   Monthly -
For a Fast & FREE Mortgage Pre-ApprovalApply Now
More Like This
  • MLS#: A4680403 ( Residential )
  • Street Address: 3435 Winding Oaks Drive 18
  • Viewed: 33
  • Price: $1,150,000
  • Price sqft: $352
  • Waterfront: No
  • Year Built: 1988
  • Bldg sqft: 3270
  • Bedrooms: 2
  • Total Baths: 3
  • Full Baths: 2
  • 1/2 Baths: 1
  • Garage / Parking Spaces: 2
  • Days On Market: 27
  • Acreage: 13.84 acres

Description

Own your own slice of tropical paradise on Longboat Key with this beautiful two bedroom two and on half bath Villa in the exclusive Winding Oaks Community located behind the gates of Bay Isles Association. Sweeping views of the Longboat Key Club Harbourside Golf Course and a sparkling inland waterway from your primary bedroom and expansive living/dining room combo that both exit through sliders to a fully enclosed wrap around deck to further enhance your tropical lifestyle. Open floor plan with soaring ceilings and enclosed atrium help to maximize the natural light and make the 2,555 sq feet feel even larger. Beautifully updated eat in kitchen with striking tray ceiling, ample pantry storage, bright white cabinets, quartz countertops and stainless steel appliances. Primary owners suite includes an designer walk in closet, updated bath with ceramic tile, walk in shower, double sinks and quartz counter tops. Split layout offers a private guest suite, with walk in closet, updated ensuite bathroom with ceramic tile, walk in shower and quartz counter tops. Large office with desk nook could easily be converted to another bedroom. Laundry room with storage and sink adjacent to large 2 car garage with epoxy floors and storage cabinets. Meticulously maintained, Impact Windows and sliders throughout, low maintenance mature plantings in private enclosed front courtyard. Dog friendly community. Beautiful updated community pool with bathrooms. Beach access via Bay Isles Beach Club which offers a private pavilion with bathrooms, volleyball, picnic tables, grills and ample parking. Low maintenance community where all exteriors and court yards are maintained by the association. Conveniently located mid key, one mile from Publix and CVS and a short drive to the restaurants and shops of St Armands and Downtown Sarasota.
Request More Information
  • All fields are required.
Features
Building and Construction
  • Covered Spaces: 0.00
  • Exterior Features: Awning(s), Courtyard, Garden, Lighting, Private Entrance, Private Yard, Sliding Doors
  • Fencing: Masonry
  • Flooring: Carpet, Tile, Vinyl, Wood
  • Living Area: 2555.00
  • Roof: Tile
School Information
  • High School: Booker High
  • Middle School: Booker Middle
  • School Elementary: Southside Elementary
Garage and Parking
  • Garage Spaces: 2.00
  • Open Parking Spaces: 0.00
  • Parking Features: Garage Door Opener
Eco-Communities
  • Water Source: Public
Utilities
  • Carport Spaces: 0.00
  • Cooling: Central Air, Humidity Control
  • Heating: Central, Electric
  • Pets Allowed: Dogs OK, Size Limit, Yes
  • Sewer: Public Sewer
  • Utilities: BB/HS Internet Available, Cable Available, Electricity Connected, Public, Sewer Connected, Underground Utilities, Water Connected
Amenities
  • Association Amenities: Pool, Vehicle Restrictions
Finance and Tax Information
  • Home Owners Association Fee Includes: Guard - 24 Hour, Cable TV, Common Area Taxes, Pool, Escrow Reserves Fund, Fidelity Bond, Maintenance Structure, Maintenance Grounds, Recreational Facilities, Trash
  • Home Owners Association Fee: 0.00
  • Insurance Expense: 0.00
  • Net Operating Income: 0.00
  • Other Expense: 0.00
  • Tax Year: 2025
Other Features
  • Appliances: Built-In Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
  • Association Name: Neil Fleet
  • Association Phone: 941-383-3200
  • Country: US
  • Furnished: Furnished
  • Interior Features: Ceiling Fans(s), Eat-in Kitchen, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Split Bedroom, Tray Ceiling(s)
  • Legal Description: UNIT 18 WINDING OAKS
  • Levels: One
  • Area Major: 34228 - Longboat Key
  • Occupant Type: Owner
  • Parcel Number: 0004121018
  • Unit Number: 18
  • View: Golf Course, Water
  • Views: 33
  • Zoning Code: MUC1
Nearby Subdivisions
Arbomar Apts   Aria Longboat Key   Bay Harbour Apts   Bayport   Bayport Bch Ten Ph D   Bayport Bch Ten Ph E   Beach Harbor Club   Beaches Of Longboat Key   Beaches Of Longboat Key Ph-1   Beaches Of Longboat Key Ph1   Beachplace 1   Beachplace I   Beachplace Ii   Beachplace Iii   Buttonwood Cove   Casa Del Mar   Cedars East Sec 2   Cedars East Sec 3   Club Longboat Beach Tennis   Coreys Landing   Covert Ii   En Provence   Fairway Bay   Fairway Bay 1   Fairway Bay 2 Ph 1   Fairway Bay 2 Ph 2 3   Fairway Bay 3   Grand Bay 1   Grand Bay 2   Grand Bay 3   Grand Bay 4   Grand Bay 5   Grand Bay 6   Harbor Oaks Ph I Ii   Harbour Villa Club At The Bucc   Inn On The Beach Ph I   Inn On The Beach Ph Ii   Inn On The Beach Ph Iii   Islander Club Of Longboat   Islands West   L Ambiance   L Ambiance 1   L Ambiance At Longboat Key Clu   La Firenza   Longbeach   Longbeach Condominius   Longboat Arms   Longboat Beach House   Longboat Harbour   Longboat Harbour Towers   Longboat Key Casa Del Mar   Longboat Key Towers   Longboat Landing   Longboat Sandpipers   Mccalls Beach Castle   Neptune On Longboat Key   Northgate Of Longboat Key   Pelican Harbour Beach Club   Pierre   Players Club   Players Club I   Players Club Iii   Players Club Iv   Portobello   Positano   Privateer North   Privateer South   Regent Place Ph 1   Saint Judes Apts   Sanctuary I   Sanctuary Ii   Sanctuary Iii   Sanctuary Iv   Sand Cay   Sands Point   Sea Gate Club   Sea Pines   Seagrape Inn   Seaplace   Seaplace I   Seaplace Ii   Seaplace Iii   Seaside Of Longboat   Spanish Main Yacht Club Condo   St. Regis Longboat Key   Sunset Beach   Sutton Place   Tangerine Bay Club   The Banyan Bay Club   The Grande At Longboat Key   Turtle Crawl Sec 36 Township 3   Veinte   Villa Di Lancia Ph 1   Villa Dos Palmas   Water Club 01 At Longboat Key   Water Club At Longboat Key   Water Club Iilongboat Key   Westchester   Westchester Apts   Whitney Beach   Winding Oaks   Windward Bay Amd  
Similar Properties

Active
Details for 7125 Gulf Of Mexico 22, Longboat Key, FL 34228
$1,250,000.00

7125 Gulf Of Mexico 22 Virtual Tour More Like This

Experience coastal living at its finest in this beautifully remodeled beachfront condo! This stunning residence features brand new, tastefully selected furniture and a modern, elegant design throughou

  1. Request Information
  1. Bedrooms: 2
  2. Baths: 2
  1. MLSID: F10536500
  2. Provided by Realty 100
  3. Provided through
  4. DMCA Notice
48 Pictures and Information
Active
Details for 4311 Gulf Of Mexico Drive 501, LONGBOAT KEY, FL 34228
$1,200,000.00 ($968.52 / sqft )

4311 Gulf Of Mexico Drive 501 Virtual Tour More Like This

PARADISE BEACHFRONT CONDO! It does not get better than this. Panoramic Gulf and Bay Views and beach views from every room. Enjoy relaxing at the beach or at the pool. This 2 bedroom, 2 bathroom condo

  1. Request Information
  1. Bedrooms: 2
  2. Baths: 2
  3. Approx. 1239 sqft
  4. Approx. 1.82 acres
  1. MLSID: A4601858
  2. Provided by SPECIALIZED REAL ESTATE LLC
  3. Contact Otto Hajek
  4. mfrmls
  5. DMCA Notice
53 Pictures and Information
Active
Details for 2675 Gulf Of Mexico Drive 403, LONGBOAT KEY, FL 34228
$1,200,000.00 ($581.96 / sqft )

2675 Gulf Of Mexico Drive 403 Virtual Tour More Like This

A New Year is here and a New Price with gorgeous full gulf views on Longboat Key. Veinte (20 in Spanish) is a luxury condominium community with only twenty residents located on beautiful and unique Lo

  1. Request Information
  1. Bedrooms: 3
  2. Baths: 2
  3. Approx. 2062 sqft
  4. Approx. 2.02 acres
  1. MLSID: A4645760
  2. Provided by COLDWELL BANKER REALTY
  3. Contact Sandra Endres
  4. mfrmls
  5. DMCA Notice
71 Pictures and Information
Active
Details for 1050 Longboat Club Road 903, LONGBOAT KEY, FL 34228
$1,100,000.00 ($728.96 / sqft )

1050 Longboat Club Road 903 Virtual Tour More Like This

SIGNIFICANT PRICE REDUCTON This TOTALLY RENOVATED ISLAND BEAUTY will charm the most sophisticated Buyers and the spectacular sunrise views over Sarasota Bay enhanced by sunset lit City and Golf Cour

  1. Request Information
  1. Bedrooms: 2
  2. Baths: 2
  3. Approx. 1509 sqft
  1. MLSID: A4647430
  2. Provided by ROSEBAY INTERNATIONAL REALTY, INC
  3. Contact Tina Rudek Stark, PA
  4. mfrmls
  5. DMCA Notice
94 Pictures and Information
Active
Details for 1000 Longboat Club Road 1105, LONGBOAT KEY, FL 34228
$1,075,000.00 ($773.38 / sqft )

1000 Longboat Club Road 1105 Virtual Tour More Like This

Rarely available and beautifully renovated 11th floor Penthouse with breathtaking Gulf, Sunset and Bay views and ideally situated within a short beach walk between the popular Resort at Longboat Key C

  1. Request Information
  1. Bedrooms: 2
  2. Baths: 2
  3. Approx. 1390 sqft
  1. MLSID: A4657701
  2. Provided by ROSEBAY INTERNATIONAL REALTY, INC
  3. Contact Tina Rudek Stark, PA
  4. mfrmls
  5. DMCA Notice
100 Pictures and Information
Active
Details for 1105 Gulf Of Mexico Drive 402, LONGBOAT KEY, FL 34228
$1,105,000.00 ($740.62 / sqft )

1105 Gulf Of Mexico Drive 402 Virtual Tour More Like This

Beachplace at Longboat Key: Gulf front luxury and rental friendly, turnkey furnished investment opportunity! An iconic condominium in the mid century modern style, Beachplace was constructed under the

  1. Request Information
  1. Bedrooms: 2
  2. Baths: 2
  3. Approx. 1492 sqft
  4. Approx. 5.01 acres
  1. MLSID: A4661696
  2. Provided by DUNCAN REAL ESTATE, INC.
  3. Contact Tom Aposporos
  4. mfrmls
  5. DMCA Notice
20 Pictures and Information
Active
Details for 1055 Gulf Of Mexico Drive 504, LONGBOAT KEY, FL 34228
$1,299,000.00 ($810.36 / sqft )

1055 Gulf Of Mexico Drive 504 Virtual Tour More Like This

This direct Gulf front residence at Beachplace offers an extraordinary opportunity to enjoy the very best of Longboat Keys beachfront lifestyle. Perfectly positioned to capture unobstructed views of t

  1. Request Information
  1. Bedrooms: 2
  2. Baths: 2
  3. Approx. 1603 sqft
  4. Approx. 7.98 acres
  1. MLSID: A4663883
  2. Provided by COLDWELL BANKER REALTY
  3. Contact Roger Pettingell
  4. mfrmls
  5. DMCA Notice
35 Pictures and Information
Active
Details for 210 Sands Point Road 2405, LONGBOAT KEY, FL 34228
$1,175,000.00 ($1,807.69 / sqft )

210 Sands Point Road 2405 Virtual Tour More Like This

Located behind the gates of the highly desirable Longboat Key Club, this 1BR/1BA Club Suite at Inn on the Beach offers a unique opportunity to own within the prestigious Longboat Key Club Resort. Span

  1. Request Information
  1. Bedrooms: 1
  2. Baths: 1
  3. Approx. 650 sqft
  1. MLSID: A4664039
  2. Provided by COLDWELL BANKER REALTY
  3. Contact Bruce Myer
  4. mfrmls
  5. DMCA Notice
36 Pictures and Information
Active
Details for 5320 Gulf Of Mexico Drive 101, LONGBOAT KEY, FL 34228
$1,150,000.00 ($869.24 / sqft )

5320 Gulf Of Mexico Drive 101 Virtual Tour More Like This

Rarely Available at Longboat Landing! This 3 bedroom, 2 bath second floor condo offers the ultimate in coastal living with only 9 total units/owners in the entire communityproviding privacy, exclusivi

  1. Request Information
  1. Bedrooms: 3
  2. Baths: 2
  3. Approx. 1323 sqft
  4. Approx. 1.53 acres
  1. MLSID: A4666843
  2. Provided by KELLER WILLIAMS ON THE WATER S
  3. Contact Schuyler Burke
  4. mfrmls
  5. DMCA Notice
37 Pictures and Information
Active
Details for 240 Sands Point Road 4205, LONGBOAT KEY, FL 34228
$1,115,000.00 ($1,742.19 / sqft )

240 Sands Point Road 4205 Virtual Tour More Like This

This junior suite, located in Building 4, offers spectacular northwest facing views of the Gulf, providing owners with breathtaking sunsets and expansive water vistas. For those seeking accommodation

  1. Request Information
  1. Bedrooms: 1
  2. Baths: 1
  3. Approx. 640 sqft
  4. Approx. 4.13 acres
  1. MLSID: A4667038
  2. Provided by PREMIER SOTHEBY'S INTERNATIONAL REALTY
  3. Contact Jackie Kleppinger
  4. mfrmls
  5. DMCA Notice
39 Pictures and Information

Contact Info

Skip to Main Content
  1. Broker IDX Sites Inc.
  2. A Winning Team
Broker IDX Billing System

Looking To Sell Your Property ?

Connecting agents, buyers, and sellers
Call Us Now Get In Touch
Featured Listings
132 Mendoza Circle
Main Stree Ne Main Street Boulevard
156 Mendoza Circle
337 Rutledge Avenue
6436 Grand Cypress Circle
535 Peninsula Avenue

Copyright ©2006-2026 brokerIDXsites.com   |   All Rights Reserved.